No guarantee that prices will keep climbing indefinitely. If anything, median asking prices seem to have flattened over the last month.

http://www.deptofnumbers.com/asking-prices/california/san-diego/

This may actually BE a good time to sell, since inventory is still tight, so you have less competition from other sellers.

As far as being a landlord, if you cash-flow, what’s wrong with being one? Let some other dumbkopf pay part of your mortgage on your new pad.